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Woodside

The bucolic town of Woodside is nestled among the redwood-covered mountains along the coastal ridge of the Peninsula, and exudes a natural warmth and rural character. The rustic downtown retains its historic feel through original architecture and storefronts, and along the downtown strip of Woodside Road is some of the best dining in the area, including the Michelin rated Village Pub. The town is perhaps best known as a haven for equestrians within the Bay Area. An integral part of the local culture, numerous residents keep their own horses, and the town hosts many horse clubs and events while maintaining a vast network of equestrian trails. Running and hiking trails abound for the outdoor enthusiast, and some of my favorite treks are in Huddart and Wunderlich parks. Woodside is also a destination for cyclists, and is often alight with bikers on some of its most popular routes including Old La Honda Road, King’s Mountain Road, and Cañada Road.

The eight day long Tour of California bicycle race even includes several roads along and adjacent to Skyline Boulevard and Highway 84. Another local treasure is Filoli, one of the finest remaining historic country estates of the early 20th century. It features a 36,000 square foot home, and world-renowned 16 acre English Renaissance garden surrounded by a 654 acre estate. Docent-guided hikes through the Filoli Nature Preserve, and summer Jazz at Filoli, are visitor’s favorites. Cycling the hills of Woodside is one my favorite activities. On weekends especially the streets are lined with cyclists, many who stop off at Buck’s restaurant after a rigorous ride through the mountains. While it is a great place for locals, this unassuming restaurant has also seen some of the most lucrative deals in Silicon Valley history discussed at its tables.